ethyl 4-C-[(S)-1-phenyl-1-hydroxymethyl]-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside

Base Information

Chemical Name:ethyl 4-C-[(S)-1-phenyl-1-hydroxymethyl]-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside
CAS No.:468076-74-6
Molecular Formula:C₁₅H₂₀O₄
Molecular Weight:264.321
Hs Code.:

Synonyms:ethyl 4-C-[(S)-1-phenyl-1-hydroxymethyl]-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of ethyl 4-C-[(S)-1-phenyl-1-hydroxymethyl]-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside

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Technology Process of ethyl 4-C-[(S)-1-phenyl-1-hydroxymethyl]-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside

There total 3 articles about ethyl 4-C-[(S)-1-phenyl-1-hydroxymethyl]-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 57.0%

: 100-52-7
benzaldehyde

: 468076-81-5
ethyl 4-bromo-2,3,4-trideoxy-α-D-erythro-hex-2-enopyranoside

: 347382-91-6
ethyl 2-C-[(S)-1-phenyl-1-hydroxymethyl]-3,4-dideoxy-α-D-threo-hex-3-enopyranoside

: 468076-74-6
ethyl 4-C-[(S)-1-phenyl-1-hydroxymethyl]-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside

Guidance literature:: With indium; In ethanol; water; at 20 ℃; for 5h;
DOI:10.1002/1615-4169(200206)344:3/4<319::AID-ADSC319>3.0.CO;2-S

Reference yield:

: 116455-00-6
Ethyl 6-O-(tert-butyldimethylsilyl)-2,3-dideoxy-α-D-threo-hex-2-enopyranoside

: 468076-74-6
ethyl 4-C-[(S)-1-phenyl-1-hydroxymethyl]-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1: Ph₃P; CBr₄ / CH₂Cl₂ / 0 °C

2: NBu₄⁽¹⁺⁾*F^(1-) / tetrahydrofuran / 3 h / 20 °C

3: 57 percent / indium powder / ethanol; H₂O / 5 h / 20 °C

With indium; carbon tetrabromide; tetrabutyl ammonium fluoride; triphenylphosphine; In tetrahydrofuran; ethanol; dichloromethane; water; 3: Barbier allylation;
DOI:10.1002/1615-4169(200206)344:3/4<319::AID-ADSC319>3.0.CO;2-S

Reference yield:

: ethyl 6-O-(tert-butyldimethylsilyl)-4-bromo-2,3,4-trideoxy-α-D-erythro-hex-2-enopyranoside

: 468076-74-6
ethyl 4-C-[(S)-1-phenyl-1-hydroxymethyl]-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside

Guidance literature:: Multi-step reaction with 2 steps

1: NBu₄⁽¹⁺⁾*F^(1-) / tetrahydrofuran / 3 h / 20 °C

2: 57 percent / indium powder / ethanol; H₂O / 5 h / 20 °C

With indium; tetrabutyl ammonium fluoride; In tetrahydrofuran; ethanol; water; 2: Barbier allylation;
DOI:10.1002/1615-4169(200206)344:3/4<319::AID-ADSC319>3.0.CO;2-S